Wanderings, musings, and assorted whatnot

On Entrepreneurship

“Entrepreneurship is jumping off a cliff and assembling a plane on the way down.”

Trueish. First you dream of flying. Then you look for the right airplane and find that there’s nothing quite right in the market. So you borrow and beg for every penny to build a sub $100,000 supersonic personal jet. You create a chart showing that the market for this is only slightly smaller than the market for hamburgers.

When you have enough money for the prototype sans engine, you push it all off the edge of the cliff and build as fast as you can. Friends see you falling and think, “man that looks so much cooler than my job.” They happily jump and start building.

Shortly, realizing you had no concept of the enormity of the task, you start screaming “help”. Strange men wearing impossibly crisp blue button downs and khakis, with perfect hair, who have no actual experience creating a successful company, will start complimenting you on how smart you were to use the radically new “Agile Cliff methodology. They follow you down in very nice business jets and start shouting strange chants with obscure opaque language that will supposedly summon great fountains of money. All you have to do is put a drop of blood on the contract, give up 51% of your company, 3 of 5 board seats and agree to use half the money to buy products you don’t understand and aren’t ready for from their “portfolio companies. With the blood and signature they move you into a building with 10 other companies falling at slower rate. You now have 12 months til death. And they tell you to stave off death for another year you need to stop working on the plane in six months and go out hat in hand begging for 10x as much money at a 10x valuation.

Nine of the ten companies hit the ground hard. The living fall into one of three categories: 1. H1B visa violators, thrown immediately out of the U.S., 2. Deeply depressed normal folk who sleep for two years and wonder why the fuck did I leave my solid job in accounting to work with these dipshits? 3. The executive staff who are proudly complimented on how elegantly they hit the ground. The blue shirts assure these folks that, “we invest in teams, in people. One little failure just put you much closer to success. Call us with your next idea.”

The one company that doesn’t hit the ground has piles of software they will never need and one prototype plane that technically does fly, but the features necessary to bring it to market are cheaper to get by buying the leading competitor in the space. You still have a million bucks in the bank and enough gas to stay aloft for nine months. You’re fucked, until your sleazy partner says, “we did not fail. Once we understood the space better we decided that there is a greater need for an airplane crash video app. As of this moment I decree us the leading predictor of cliff jumping deaths and airplane crash videos for new media. He holds up the contract he just signed with his Aunt’s knitting blog for being sole supplier of death and dismemberment content for the entire knitting world. After an excruciating pause everyone around the table agrees that a “pivot” sounds much better than saying, “we were naive and stupid and failed completely. But we are immensely smarter than we were.”

Bizarrely the Pivot press release gets picked up by ten times as many tech rags as even heard of your first attempt. They use the word pivot awkwardly and endlessly in such an ungainly fashion that you realize that they are too young to have seen the Friends episode where Ross moves a couch. If they had seen it they would never have said the word again.

And the true entreupeneur begins to climb that cliff again. Because he knows he is Syssiphus with better ideas and the laptop he stole as he left the plane. “For I will jump again, I have no choice, it is who I am.”

Tl;dr Most Entreupeneurs are naive and foolish and fail painfully. Occasionally one sort of succeeds and gets great press coverage. One out of every 100,000 succeeds so fabulously that it makes the whole category of work look incredibly cool. But you are a nerd and should never listen when told you are cool.